Got in on an Internet IPO during the dotcom bubble of 1998-99. I was eligible to buy 100 shares at the IPO price of 19, which I did, then almost immediately sold for 61 on the first day of trading. Made over $4,000 in a few minutes.

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__________________"Hey, for every ten dollars, that's another hour that I have to be in the work place. That's an hour of my life. And my life is a very finite thing. I have only 'x' number of hours left before I'm dead. So how do I want to use these hours of my life? Do I want to use them just spending it on more crap and more stuff, or do I want to start getting a handle on it and using my life more intelligently?"-- Joe Dominguez (1938 - 1997)

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I once made (won) almost 70k in two hours at one casino. I've made 30 to 40k in one day playing at casinos several times. (All table games) Since you didn't ask about short term losses, I'll not common on those, but they far exceed the wins.

two very nice wins one at 20/1 another at 25/1 ( bizarrely i considered both a 'sure thing ' other gamblers didn't , so the price drifted out and the horses bolted in convincingly) but that was my younger days

but i suppose to OP meant the share market

one was (is i still hold a few ) a micro cap i bought in @ at 0.1c in Sept. 2016 when it announced a change of focus into selling Australian wine online into ( mostly ) China

a few months later it added a digital currency play the last of several sell-downs was at 1.5c in November 2017 that share is currently in a prolonged trading halt as the regulator comes to grips with digital currency trading as a financial business

the last official price was 0.9c ( but i already had taken plenty of profit )

( i have a motto of NOT being overly greedy )

another was bought into as a micro cap oil play bought at 1.4c ( a new share ) it started producing some oil ( but probably not in a persistent profit ) and decided to plunge into IT security ( and was eventually a reverse take-over ) my last share sell-down ( of several ) was at 46.5c in October 2015 , the share is still currently trading @ roughly 38c but is now trying to be a internet bank and money transfer facility

the stand-out is a share Pro Medicus ( some US folks might have heard of that one , any medical professionals as members ?) bought @ 16.5c in June 2011

the last sell down ( of several ) was @ $3.02 in December 2015

i still hold some ( a top 10 holding ) and is currently trading in excess of $19 ( the peak so far is $20.52 )

a teenage nick-name used to be 'lucky ' ( that morphed over the decades ) maybe one of my friends was a visionary .

HOWEVER my key goal is a robust source of income in my retirement ( i am hoping to never having to draw-down on investment capital )

such lucky moments have to be limited so as not to lose focus on the main task

i believe in taking profits at sensible levels ( and reinvesting them sensibly )

please note all share prices are in Australian dollars ( and cents )

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i hold the Australian listed versions of BHP , and JHG .

You must learn from the mistakes of others. You can't possibly live long enough to make them all yourself.

Being an active investor, I routinely make (and lose) $50k to $100k on short-term bets. This amount does not include the gain or loss on my core holdings whose fluctuating values far exceeded the amount above.

When I "lost" in a short-term bet, I just waited it out and it became a long-term stock AA increase.

Thus, it is not the same as losing in Las Vegas, where the lost money would never come back to you.

__________________"Old age is the most unexpected of all things that can happen to a man" -- Leon Trotsky

A week after moving to PA, I had nothing to do, my family was still in California, so I drove to Atlantic City for a one night stay. I gambled a little in the evening, and again late the next morning. I was about even the early in the afternoon and needed to leave for my 3 hr drive home, but really wanted to spend a little time on the Quarter Wheel of Fortune slot machines. I gave myself a 20 minute window, no more than $40, then planned to leave.

None of the machines were available. I went to a nearby bank of nickel machines, threw in a $5 bill, and hit a jackpot for $20 before I had spent $2. I cashed out there, went back to to the Wheel of Fortune machines-still none available. So hanging out nearby, I tried a dime machine with my $20. After about 5 pulls, the machine started clanging and flashing. I won a $1400 progressive. After giving the casino folks the form for taxes, I decided to go to the dollar Wheel if Fortune machines, then go home after 5 minutes. In those 5 minutes, only putting in a $20, I walked away with another $400. That $1800 cash, won within in my allotted 20 minutes, was my cash stash for months.

This is reminding me of my favorite quick score story.
My grandparents retired at 65 (which is what you did in those days) and decided to fulfill their lifetime dream of a driving trip to see the United States (which was smaller back then -- only 48 states).

They had a great trip and eventually came to Las Vegas. Their room wasn't ready so they had a few hours to kill in a casino. Within an hour they were up over $6,000 (over $50,000 today). Grandma was having such a wonderful time she wanted to keep at it, but Grandpa took her by the arm and steered her out to the parking lot. "Shouldn't we see if our room is ready yet?" she asked.
"No, we're getting out of this town as fast as we can and never coming back." he replied.

My grandfather only had about five years of grade school but he was a very smart cookie.

I remember the flash crash of 2015. I was watching the screen and the numbers made no sense, down SO much in a few minutes. Unfortunately I didn't buy anything, if I did I would have made a easy 20% in a few minutes.

Some gambling - $2 Powerball Ticket yields $50K (before taxes) - it's funny - I actually have ties with 3 people who I knew directly or have won the lottery - one was a classmate I went to High School with, 1 was a former co-worker's father, 1 went to high school with of one my managers (a neighboring school district). Nice to see somebody wins!

I like the horse racing claimer story - I thought claimers were a real grind but it looks like you found a good one to make a good short-term return - I am a sports card enthusiast and the guy I usually buys cards from has a couple of horses - he buys yearlings and he said it is a fun hobby but he's happy if he just breaks even but he's in the game and he enjoys it. He told me the medical costs for the horses can be expensive (and they are unplanned).

Good to see somebody caught the meat substitute stock - interesting company - and then you have Enron...that really took me back. Thanks for sharing your stories. I enjoyed reading.

I bought some in early 2000. My skeptical self got nervous about it and sold it later that year for about an 18% gain. Not a big sum, but I've always felt good about it, and even today I smile whenever I hear Enron mentioned.

I wondered if I was the only one who made out on Enron. I gambled on the free fall @ around $.60 / shr. Sold for $.90 a few days later. Never went back in...

Now that I think about it, Nortel, QCOM, BRCM, dotcom days were exciting.

We also bought a house for $282k in 2015. Sold it for $428k in 2.5 years. Next home was $282k ironically, 2 streets over, albeit smaller. I think we netted $100k after all the dust settled... Tax free, of course.

I bought some penny stock @ 7 cents and sold out at 60 cents after turning my initial purchase into a free trade, and put the initial purchase money into BRK.B. After I sold out I read a story about how some guy was able to get home from the Greek islands because he had BTC. It was 2015 I think when Greece froze up and nothing worked BUT BTC. I decided I needed some of that so I took the profit from the penny stock and put half in BRK.B and half in BTC @ $275. BRK.B is up 26% since I bought it, and BTC is up 2900%

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